When the herd was on the move, Smith frequently anticipated their progress and galloped up ahead to choose a good vantage point from which to photograph. He also documented the various positions the day herders took to guide the cattle along the trail, from those riding "point" to the "drags" that followed the herd to keep stragglers from falling too far behind. At night, he photographed night herders being awakened to take their posts guarding the herd.

The era of massive trail drives was already over when Smith began documenting the life of the cowhand. The long drives had been supplanted by the railroads, which could move large numbers of cattle across the country much faster. Smith chose to work with bigger outfits, however, so that his photographs would capture at least a sense of what the earlier drives must have been like. In 1910, Smith was able to document the Matador outfit's fall trail drive to the newly constructed cattle pens at the railhead in Lubbock, Texas. No photographer had ever documented a cattle drive from beginning to end.